N-Methoxy-N-methylacetamide Chemical Properties

Boiling point:

152 °C (lit.)

Density 

0.97 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.426(lit.)

Flash point:

121 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Colorless

Water Solubility 

Soluble

InChI

InChI=1S/C4H9NO2/c1-4(6)5(2)7-3/h1-3H3

InChIKey

OYVXVLSZQHSNDK-UHFFFAOYSA-N

SMILES

C(N(OC)C)(=O)C

CAS DataBase Reference

78191-00-1(CAS DataBase Reference)

Safety Information

Risk Statements 

10

Safety Statements 

16-24/25

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29280000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

N-Methoxy-N-methylacetamide Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

N-Methoxy-N-methylacetamide, is a Weinreb amide used in the synthesis of marine natural products myriaporone and usneoidone as a ketone synthon.

Preparation

N-Methoxy-N-methylacetamide can be prepared by reaction of Acetyl Chloride with commercially available N,O-Dimethylhydroxylamine hydrochloride in pyridine, followed by distillation at reduced pressure (65%).

General Description

Simple Weinreb amide used in the synthesis of marine natural products myriaporone and usneoidone as a ketone synthon.

Synthesis

N-Methoxy-N-methylacetamide (105) was synthesized as follows: pyridine (10 mL, 124 mmol) was slowly added dropwise to a well-stirred suspension of O,N-dimethylhydroxylamine hydrochloride (6 g, 62 mmol) and acetyl chloride (4.15 mL, 59 mmol) in dichloromethane (85 mL) under argon protection. The reaction mixture was gradually warmed to room temperature and stirred continuously for 3 hours. Subsequently, the reaction mixture was partitioned between brine (55 mL) and ether (85 mL). The aqueous phase was extracted with additional ether and the combined organic layers were dried over anhydrous sodium sulfate, concentrated and purified by reduced pressure distillation to afford Weinreb amide 105 (4.54 g, 72% yield) as a colorless liquid. The boiling point of the product was 42-44 °C/20 mmHg; IR (pure sample) showed absorption peaks located at 3497, 2971, 2941, 2824, 1663 cm-1; 1H NMR (CDCl3, 300 MHz) δ 3.62 (s, 3H), 3.11 (s, 3H), 2.05 (s, 3H); 13C NMR (CDCl3. 75.4 MHz) δ 171.8 (C), 61.0 (CH3), 31.9 (CH3), 19.6 (CH3). The spectral data of the obtained products are in agreement with literature reports.

storage

N-Methoxy-N-methylacetamide is stable but should be protected from moisture; use in a fume hood.

References

[1] Organic Letters, 2012, vol. 14, # 9, p. 2250 - 2253
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 2, p. 278 - 286
[3] Patent: EP1300403, 2003, A1
[4] Tetrahedron Letters, 1983, vol. 24, # 18, p. 1851 - 1854
[5] Tetrahedron Letters, 2007, vol. 48, # 3, p. 377 - 380

N-Methoxy-N-methylacetamide(78191-00-1)Related Product Information

• N-Methylacetamide
• Thioacetamide
• 2-Methoxyethanol
• Acetamide
• (Trifluoromethoxy)benzene
• Anisole
• N-Chlorosuccinimide
• N,N-Dimethylacetamide
• N,N'-Disuccinimidyl carbonate
• GMBS
• SPDP
• N-(Benzyloxycarbonyloxy)succinimide
• BOC-TRP-OSU
• BOLTON-HUNTER REAGENT
• N-Succinimidyl S-Acetylthioglycolate
• N-(2-Chlorobenzyloxycarbonyloxy)succinimide
• Fmoc-OSu
• SMCC crosslinker